Copper(I)-Catalyzed Click Chemistry as a Tool for the Functionalization of Nanomaterials and the Preparation of Electrochemical (Bio)Sensors

Yáñez‐Sedeño, Paloma; González‐Cortés, Araceli; Campuzano, Susana; Pingarrón, José M.

doi:10.3390/s19102379

Cited by 29 publications

(18 citation statements)

References 84 publications

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“…Furthermore, the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) has a great variety of possibilities in electrochemical biosensors [ 73 ]. To overcome the long time needed for chemical generation of the cuprous ion (~16 h), the electrogeneration of the catalyst by applying a previously optimized reduction potential for a fixed time (~300 s) has been exploited, leading to a methodology known as electroclick chemistry that provides good results in the preparation of biosensors [ 59 , 74 ].…”

Section: Bioelectroanalytical Methods For the Determination Of Infmentioning

confidence: 99%

Revisiting Electrochemical Biosensing in the 21st Century Society for Inflammatory Cytokines Involved in Autoimmune, Neurodegenerative, Cardiac, Viral and Cancer Diseases

Campuzano

Yáñez‐Sedeño

Pingarrón

2020

Sensors

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The multifaceted key roles of cytokines in immunity and inflammatory processes have led to a high clinical interest for the determination of these biomolecules to be used as a tool in the diagnosis, prognosis, monitoring and treatment of several diseases of great current relevance (autoimmune, neurodegenerative, cardiac, viral and cancer diseases, hypercholesterolemia and diabetes). Therefore, the rapid and accurate determination of cytokine biomarkers in body fluids, cells and tissues has attracted considerable attention. However, many currently available techniques used for this purpose, although sensitive and selective, require expensive equipment and advanced human skills and do not meet the demands of today’s clinic in terms of test time, simplicity and point-of-care applicability. In the course of ongoing pursuit of new analytical methodologies, electrochemical biosensing is steadily gaining ground as a strategy suitable to develop simple, low-cost methods, with the ability for multiplexed and multiomics determinations in a short time and requiring a small amount of sample. This review article puts forward electrochemical biosensing methods reported in the last five years for the determination of cytokines, summarizes recent developments and trends through a comprehensive discussion of selected strategies, and highlights the challenges to solve in this field. Considering the key role demonstrated in the last years by different materials (with nano or micrometric size and with or without magnetic properties), in the design of analytical performance-enhanced electrochemical biosensing strategies, special attention is paid to the methods exploiting these approaches.

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Section: Bioelectroanalytical Methods For the Determination Of Infmentioning

confidence: 99%

Revisiting Electrochemical Biosensing in the 21st Century Society for Inflammatory Cytokines Involved in Autoimmune, Neurodegenerative, Cardiac, Viral and Cancer Diseases

Campuzano

Yáñez‐Sedeño

Pingarrón

2020

Sensors

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“…Alternatively, coupling between single amino acid residues present or introduced on the surface of proteins and corresponding chemical functions on electrodes can be realized [2]. In most cases, cysteine (Cys) is the Non canonical amino acids (NAA) can be incorporated in any place of a redox enzyme, contrary to His-tag [56]. NAA library offers a great versatility already largely exploited in protein-protein interaction biological studies.…”

Section: Protein Engineering For Specific Recognition Of Functionalizmentioning

confidence: 99%

Recent advances in surface chemistry of electrodes to promote direct enzymatic bioelectrocatalysis

Mazurenko

Hitaishi

Lojou

2020

Current Opinion in Electrochemistry

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Redox enzymes catalyze major reactions in microorganisms to supply energy for life. Their use in electrochemical biodevices requires their integration on electrodes, while maintaining their activity and optimizing their stability. In return, such applicative development puts forward the knowledge on involved catalytic mechanisms, providing a direct electrode connection of the enzyme is fulfilled. Enzymes being large molecules with active site embedded in an insulating moiety, direct bioelectrocatalysis supposes strategies for specific orientation of the enzyme to be developed. In this review, we summarize recent advances during the past three years in the chemical modification of electrodes favoring direct electrocatalysis. We present the different methodologies used according to the electrode materials, including metals, carbon-based electrodes or porous structures, and discuss the gained insights into bioelectrocatalysis. We especially focus on enzyme engineering which appears as an emerging strategy for enzyme anchoring. Remaining challenges will be discussed with regards to these last findings.

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“…The CuAAC of organic azides and terminal alkynes is considered to be a versatile and promising approach to prepare new bioactive compounds, pharmaceutical lead compounds, bio-probes, soft materials among others [45][46][47][48][49][50].…”

Section: Cuaac Of Azidoethyl-nitroindazoles With Terminal Alkynesmentioning

confidence: 99%

A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions

et al. 2019

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The alkylation of a series of nitroindazole derivatives with 1,2-dibromoethane afforded the corresponding N-(2-bromoethyl)and N-vinyl-nitro-1H-indazoles. The Cu(I)-catalysed azide-alkyne 1,3-dipolar cycloaddition was selected to substitute the nitroindazole core with 1,4-disubstituted triazole units after converting one of the N-(2-bromoethyl)nitroindazoles into the corresponding azide. The reactivity in 1,3-dipolar cycloaddition reactions with nitrile imines generated in situ from ethyl hydrazono-α-bromoglyoxylates was studied with nitroindazoles bearing a vinyl unit. The corresponding nitroindazole-pyrazoline derivatives were obtained in good to excellent yields.Molecules 2020, 25, 126 2 of 18 antipyretic, antioxidant, antiparasitic, antimicrobial, antitumoral and anti-inflammatory activities, among others [5][6][7][21][22][23].Indazoles are another important group of N-heterocycles with significant biological activities as nitric oxide synthase (NOS) inhibitors, kinase inhibitors, anti-inflammatory, anticancer, antimicrobial, antifungal, antimalarial, and antileishmanial agents, among others.Some anticancer and anti-inflammatory drugs based in indazole scaffolds are commercially available [24][25][26][27][28][29][30]. Besides the biological properties presented by indazole derivatives, this family of N-heterocycles also showed potential to be used in other fields as corrosion inhibitors, components for OLEDs and battery applications, and as copolymerizing molecules for new materials [31][32][33][34].Following our interest on developing synthetic approaches to functionalize the indazole core [35,36], we decided to follow the 1,3-dipolar cycloaddition methodology to substitute nitroindazoles with triazole or pyrazoline moieties, aiming in such way to obtain new compounds with improved biological features for different applications. In the strategy envisaged it was considered that the alkylation of indazole with 1,2-dibromoethane using liquid-liquid phase transfer catalysis, could afford not only the N-1and N-2-bromoethylindazoles, but also the corresponding N-1and N-2-vinylindazoles [37]. The annular tautomerisation of two nitrogen atoms (N-1, N-2) present in the indazole ring, has been explored in synthetic and theoretical studies concerning the substitution of N-H-indazole [38]. More recently, it was reported by our group that the reactivity of N-1 and N-2 alkylated indazole isomers is strongly dependent on the reaction conditions, namely, solvent proticity and pH, as well as, electronic and steric effects [39,40].Herein it is described the synthesis of a series of N-bromoethyl-nitroindazoles and N-vinyl-nitroindazoles reacting the corresponding nitroindazoles with 1,2-dibromoethane. A detailed analysis of the reaction conditions allowed to develop a simple, fast and inexpensive protocol to obtain both the vinyl and the bromoethyl derivatives in just one step in reasonable amounts. One of the bromoethyl derivatives was used to afford the corresponding azide, and its reactivity in CuAAC reactions with different...

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Copper(I)-Catalyzed Click Chemistry as a Tool for the Functionalization of Nanomaterials and the Preparation of Electrochemical (Bio)Sensors

Cited by 29 publications

References 84 publications

Revisiting Electrochemical Biosensing in the 21st Century Society for Inflammatory Cytokines Involved in Autoimmune, Neurodegenerative, Cardiac, Viral and Cancer Diseases

Revisiting Electrochemical Biosensing in the 21st Century Society for Inflammatory Cytokines Involved in Autoimmune, Neurodegenerative, Cardiac, Viral and Cancer Diseases

Recent advances in surface chemistry of electrodes to promote direct enzymatic bioelectrocatalysis

A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions

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